Fungicidal active compound combinations

ABSTRACT

There are described new active compound combinations of a compound of the formula (I) ##STR1## with known fungicidal active compounds, and their use for the control of phytopathogenic fungi.

This application is a divisional of application Ser. No. 08/629,245filed on Apr. 8, 1996, now U.S. Pat. No. 5,672,619, which is a divisionof application Ser. No. 08/462,408 filed on Jun. 5, 1995, now U.S. Pat.No. 5,532,262, which is a continuation of application Ser. No.08/232,923 filed on Apr. 25, 1994, now abandoned.

The present application relates to novel active compound combinationswhich consist of a compound of the formula I ##STR2## on the one handand other known fungicidal active compounds on the other hand and arevery highly suitable for the control of phytopathogenic fungi.

It is already known that the compounds of the formula (I) has fungicidalproperties (cf. EP-A 339,418). The activity of this substance is good;however, in some cases it leaves something to be desired at lowapplication rates.

It is also already known that numerous azole derivatives, aromaticcarboxylic acid derivatives, morpholine compounds and other heterocyclescan be employed for the control of fungi (cf. K. H. Buchel"Pflanzenschutz und Schadlingsbekampfung" Plant protection and pestcontrol! pages 87, 136, 140, 141 and 146 to 153, Georg Thieme Verlag,Stuttgart 1977).

The action of the substances concerned, however, is not alwayssatisfactory at low application rates.

It has now been found that the new active compound combinations of acompound of the formula I ##STR3## and (A) dichlofluanid of the formula##STR4## and/or (B) tolylfluanid of the formula ##STR5## and/or (C)tetrachloro-isophthalo-dinitrile of the formula ##STR6## and/or (D)propineb of the formula ##STR7## and/or (E) tetramethyl-thiuramdisulphide of the formula ##STR8## and/or (F) mancozeb of the formula##STR9## and/or (G) anilazine of the formula ##STR10## and/or (H) copperoxychloride

and/or

(I) captan of the formula ##STR11## and/or (K) a morpholine derivativeof the formula ##STR12## and/or (L) dithianone of the formula ##STR13##and/or (M) phaltan of the formula ##STR14## and/or (N) cymoxanil of theformula ##STR15## and/or (O) methyl benzimidazole-2-carbamate of theformula ##STR16## and/or (P) fosetyl of the formula ##STR17## or itsaluminium adduct and/or (Q) metalaxyl of the formula ##STR18## and/or(R) oxadixyl of the formula ##STR19## and/or (S) fluazinam of theformula ##STR20## and/or (T)1-(4-chlorophenyl)-4,4-dimethyl-3-(1,2,4-triazol-1-yl-methyl)-pentan-3-olof the formula ##STR21## and/or (U) an azole derivative of the formula##STR22## and/or (V) an azole derivative from the group consisting of

a) difenconazole

b) penconazole

c) flusilazole

d) hexaconazole

e) myclobutanil

f) prochloraz

g) fluquinconazole

h) epoxiconazole

i) fenpropidin

j) perifenox

k) 8-t-butyl-2-(N-ethyl-N-n-propylamino)-methyl-1,4-dioxaspiro4,5!decane

and/or

(W) metiram

and/or

(X) pyrimethanil

and/or

(Y) diethofencarb

and/or

(Z) mepanipyrim and/or cyprodinyl

and/or

(α) phenylpyrrole

and/or

(β) iprodione

and/or

(Γ) vinclozolin

and/or

(δ) procymidone

and/or

(ε) benomyl

and/or

(Θ) thiphanate and/or thiophanate-methyl

and/or

(II) sulphur

and/or

(n) compounds of the formula ##STR23## have very good fungicidalproperties.

The active compound of the formula (I) is known (EP-A-339,418). Thecomponents additionally present in the combinations according to theinvention are also known.

In addition to the active compound of the formula (I), the activecompound combinations according to the invention contain at least oneactive compound from the compounds of the groups (A) to (II). They mayalso moreover contain further fungicidally active admixed components.

If the active compounds are present in the active compound combinationsaccording to the invention in certain weight ratios, the synergisticeffect is seen particularly distinct. However, the weight ratios of theactive compounds in the active compound combinations can be varied witha relatively wide range. In general, the following are proportioned to 1part by weight of active compound of the formula (I)

0.5 to 50 parts by weight, preferably

0.5 to 10 parts by weight of active compound propineb (D)

0.5 to 50 parts by weight, preferably

0.5 to 10 parts by weight of active compound mancozeb (F)

0.5 to 50 parts by weight, preferably

0.5 to 10 parts by weight of active compound TMTD (E)

0.5 to 50 parts by weight, preferably

0.5 to 10 parts by weight of active compound metiram (W)

0.5 to 50 parts by weight, preferably

0.5 to 20 parts by weight of active compound dichlofluanid (A)

0.5 to 50 parts by weight, preferably

0.5 to 20 parts by weight of active compound tolylfluanid (B)

0.5 to 50 parts by weight, preferably

0.5 to 20 parts by weight of active compound phaltan (M)

0.5 to 50 parts by weight, preferably

0.5 to 20 parts by weight of active compound captan (I)

1 to 50 parts by weight, preferably

1 to 20 parts by weight of active compound Cu oxychloride (H)

1 to 50 parts by weight, preferably

1 to 20 parts by weight of active compound sulphur (II)

0.5 to 50 parts by weight, preferably

0.5 to 10 parts by weight of active compound anilazine (G)

0.5 to 50 parts by weight, preferably

0.5 to 10 parts by weight of active compound chlorothalonil (C)

0.5 to 50 parts by weight, preferably

0.5 to 10 parts by weight of active compound dithianon (L)

0.1 to 10 parts by weight, preferably

0.5 to 5 parts by weight of active compound fluazinam (S)

0.1 to 10 parts by weight, preferably

0.5 to 5 parts by weight of active compound pyrimetanil (X)

0.1 to 10 parts by weight, preferably

0.5 to 5 parts by weight of active compound diethofencarb (Y)

0.1 to 10 parts by weight, preferably

0.5 to 5 parts by weight of active compound mepanipyrin (Z)

0.1 to 10 parts by weight, preferably

0.5 to 5 parts by weight of active compound phenylpyrrole (Saphire) (α)

0.1 to 20 parts by weight, preferably

0.5 to 10 parts by weight of active compound iprodione (β)

0.1 to 20 parts by weight, preferably

0.5 to 10 parts by weight of active compound vinclozolin (γ)

0.1 to 20 parts by weight, preferably

0.5 to 10 parts by weight of active compound procymidone (δ)

0.1 to 10 parts by weight, preferably

0.25 to 5 parts by weight of active compound benomyl (ε)

0.1 to 10 parts by weight, preferably

0.25 to 5 parts by weight of active compound carbenxazim (O)

0.1 to 10 parts by weight, preferably

0.25 to 5 parts by weight of active compound thiopanate-methyl (ω)

0.1 to 10 parts by weight, preferably

0.25 to 5 parts by weight of active compound cymoxanil (N)

0.1 to 10 parts by weight, preferably

0.25 to 5 parts by weight of active compound metalaxyl (Q)

0.1 to 10 parts by weight, preferably

0.25 to 5 parts by weight of active compound oxadixyl (R)

0.1 to 10 parts by weight, preferably

0.2 to 5 parts by weight of active compound dimethomorph (K)

0.1 to 20 parts by weight, preferably

0.2 to 10 parts by weight of active compound Al fosethyl (P)

0.01 to 10 parts by weight, preferably

0.025 to 5 parts by weight of active compound tebuconazole (T)

0.01 to 10 parts by weight, preferably

0.025 to 5 parts by weight of active compound triadimefon (U XIXc)

0.01 to 10 parts by weight, preferably

0.025 to 5 parts by weight of active compound triadimenol (U XIXa)

0.01 to 10 parts by weight, preferably

0.025 to 5 parts by weight of active compound bitertanol (U XIXb)

0.01 to 10 parts by weight, preferably

0.025 to 5 parts by weight of active compound difenconazole (Va)

0.01 to 10 parts by weight, preferably

0.025 to 5 parts by weight of active compound penconazole (Vb)

0.01 to 10 parts by weight, preferably

0.025 to 5 parts by weight of active compound flusilazole (Vc)

0.01 to 10 parts by weight, preferably

0.025 to 5 parts by weight of active compound hexaconazole (Vd)

0.01 to 10 parts by weight, preferably

0.025 to 5 parts by weight of active compound myclobutanil (Ve)

0.01 to 10 parts by weight, preferably

0.025 to 5 parts by weight of active compound prochloraz (Vf)

0.01 to 10 parts by weight, preferably

0.025 to 5 parts by weight of active compound of formula (ηa)

0.01 to 10 parts by weight, preferably

0.025 to 5 parts by weight of active compound of formula (ηb)

The active compound combinations according to the invention have verygood fungicidal properties and can be employed in particular for thecontrol of phytopathogenic fungi, such as Plasmodiophoromycetes,Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes,Deuteromycetes etc.

The active compound combinations according to the invention are veryparticularly suitable for the control of cereal diseases, such asErysiphe, Cochliobolus, Pyrenophora and Leptosphaeria, and againstfungal attack on vegetables, grapes and fruit, for example againstVenturia on apples, Botrytis on beans and Phytophthora on tomatoes.

The good plant tolerability of the active compound combinations in theconcentrations necessary for the control of plant diseases enables atreatment of above-ground parts of plants, of plants and seeds, and ofthe soil.

The active compound combinations according to the invention can beconverted into the customary formulations, such as solutions, emulsions,suspensions, powders, foams, pastes, granules, aerosols, very finecapsules in polymeric substances and in coating compositions for seeds,as well as ULV formulations.

These formulations are produced in a known manner, for example by mixingthe active compounds or the active compound combinations with extenders,that is, liquid solvents, liquefied gases under pressure, and/or solidcarriers, optionally with the use of surface-active agents, that is,emulsifying agents and/or dispersing agents, and/or foam-forming agents.In the case of the use of water as an extender, organic solvents can,for example, also be used as auxiliary solvents. As liquid solvents,there are suitable in the main: aromatics, such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics or chlorinated aliphatichydrocarbons, such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, forexample mineral oil fractions, alcohols, such as butanol or glycol aswell as their ethers and esters, ketones, such as acetone, methyl ethylketone, methyl isobutyl ketone or cyclohexanone, strongly polarsolvents, such as dimethylformamide and dimethyl sulphoxide, as well aswater. By liquefied gaseous extenders or carriers are meant liquidswhich are gaseous at ambient temperature and under atmospheric pressure,for example aerosol propellants, such as halogenated hydrocarbons aswell as butane, propane, nitrogen and carbon dioxide. As solid carriersthere are suitable: for example ground natural minerals, such askaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite ordiatomaceous earth, and ground synthetic minerals, such ashighly-disperse silica, alumina and silicates. As solid carriers forgranules there are suitable: for example crushed and fractionatednatural minerals such as calcite, marble, pumice, sepiolite anddolomite, as well as synthetic granules of inorganic and organic meals,and granules of organic material such as sawdust, coconut shells, maizecobs and tobacco stalks. As emulsifying and/or foam-forming agents thereare suitable: for example non-ionic and anionic emulsifiers, such aspolyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers,for example alkylaryl polyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates as well as albumen hydrolysis products. Asdispersing agents there are suitable: for example lignin-sulphite wasteliquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other additives can bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations in general contain between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

The active compound combinations according to the invention can bepresent in the formulations as a mixture with other known activecompounds, such as fungicides, insecticides, acaricides and herbicides,as well as in mixtures with fertilizers or plant growth regulators.

The active compound combinations can be used as such or in the form oftheir formulations or the use forms prepared therefrom, such asready-to-use solutions, emulsifiable concentrates, emulsions,suspensions, wettable powders, soluble powders and granules.

They are used in the customary manner, for example by watering,spraying, atomizing, scattering, dusting, brushing on, as a powder fordry seed treatment, as a solution for seed treatment, as a water-solublepowder for seed treatment, as a water-dispersible powder for slurrytreatment, or seed-coating.

In the treatment of parts of plants, the active compound concentrationsin the use forms can be varied within a substantial range. They are, ingeneral, between 1 and 0.0001% by weight, preferably between 0.5 and0.001%.

In the treatment of seed, amounts of active compound of 0.001 to 50 gper kilogram of seed, preferably 0.01 to 10 g, are generally required.

For the treatment of soil, active compound concentrations of 0.00001 to0.1% by weight, preferably 0.0001 to 0.02% by weight, are required atthe site of action.

The good fungicidal action of the active compound combinations accordingto the invention can be seen from the following Examples. While theindividual active compounds have weaknesses in their fungicidal action,the combinations exhibit an action which extends beyond a simpleadditive action.

A synergistic effect is always present with fungicides if the fungicidalaction of the active compound combinations is greater than the sum ofthe actions of the individually applied active compounds.

The action to be expected for a given combination of two activecompounds can be calculated (cf. Colby, S. R., "Calculating Synergisticand Antagonistic Responses of Herbicide Combinations", Weeds 15, pages20-22, 1967) as follows:

If

x denotes the degree of efficacy, expressed in % of the untreatedcontrol, on use of the active compound A at a concentration of m ppm,

Y denotes the degree of efficacy, expressed in % of the untreatedcontrol, on use of the active compound B at a concentration of m ppm,

E denotes the expected degree of efficacy, expressed in % of theuntreated control, on use of the active compound A and B at aconcentrations of m and n ppm,

then ##EQU1##

If the actual fungicidal action is larger than calculated, thecombination is superadditive in its action, i.e. a synergistic effect ispresent. In this case, the actually observed degree of efficacy must begreater than the value for the expected degree of efficacy (E)calculated from the abovementioned formula.

EXAMPLE 1

Botrytis Test (bean)/Protective

To produce a suitable preparation of active compound, commerciallyavailable active compound formulations (individual active compounds oractive compound combinations) are diluted with water to the desiredconcentration in each case.

To test for protective activity, young plants are sprayed with thepreparation of active compound until dripping wet. After the spraycoating has dried on, 2 small pieces of agar covered with Botrytiscinerea are placed on each leaf. The inoculated plants are placed in adarkened humid chamber at 20° C.

3 days after the inoculation, the size of the infected spots on theleaves is evaluated.

In order to demonstrate synergism between the active compounds used inthis test, the results were assessed by the method described by Colby(see above).

Active compounds, active compound concentrations and test results can beseen from the following tables.

                  TABLE 1    ______________________________________    Botrytis test (bean)/protective    ______________________________________                              Degree of                 Active compound                              effectiveness                 concentration                              in % of the    Active compound                 in ppm       untreated control    ______________________________________    (I)          5            51    1 #STR24##    Dichlofluanid                 100          32    2 #STR25##    Mixture according to the invention    3 #STR26##    Expected value, calculated by the                            67    Colby formula (see above)    ______________________________________                              Degree of                 Active compound                              effectiveness                 concentration                              in % of the    Active compound                 in ppm       untreated control    ______________________________________    (I)          5            51    1 #STR27##    Procymidone  50           44    4 #STR28##    Mixture according to the invention    5 #STR29##    Expected value, calculated by the                            73    Colby formula (see above)    ______________________________________                              Degree of                 Active compound                              effectiveness                 concentration                              in % of the    Active compound                 in ppm       untreated control    ______________________________________    (I)          5            51    1 #STR30##    Phaltan      50           0    6 #STR31##    Mixture according to the invention    7 #STR32##    Expected value, calculated by the                            51    Colby formula (see above)    ______________________________________                              Degree of                 Active compound                              effectiveness                 concentration                              in % of the    Active compound                 in ppm       untreated control    ______________________________________    (I)          5            51    1 #STR33##    Fluazinam    5            20    8 #STR34##    Mixture according to the invention    9 #STR35##    Expected value, calculated by the                            61    Colby formula (see above)    ______________________________________                              Degree of                 Active compound                              effectiveness                 concentration                              in % of the    Active compound                 in ppm       untreated control    ______________________________________    (I)          5            51    1 #STR36##    Pyrimethanil 10           0    0 #STR37##    Mixture according to the invention    1 #STR38##    Expected value, calculated by the                            51    Colby formula (see above)    ______________________________________                              Degree of                 Active compound                              effectiveness                 concentration                              in % of the    Active compound                 in ppm       untreated control    ______________________________________    (I)          5            51    1 #STR39##    Carbendazim  5            52    2 #STR40##    Mixture according to the invention    3 #STR41##    Expected value, calculated by the                            76    Colby formula (see above)    ______________________________________                              Degree of                 Active compound                              effectiveness                 concentration                              in % of the    Active compound                 in ppm       untreated control    ______________________________________    (I)          5            51    1 #STR42##    Tolylfluanid 50           32    4 #STR43##    Mixture according to the invention    5 #STR44##    Expected value, calculated by the                            67    Colby formula (see above)    ______________________________________                              Degree of                 Active compound                              effectiveness                 concentration                              in % of the    Active compound                 in ppm       untreated control    ______________________________________    (I)          5            51    1 #STR45##    Chlorothalonil                 200          37    6 #STR46##    Mixture according to the invention    7 #STR47##    Expected value, calculated by the                            69    Colby formula (see above)    ______________________________________

EXAMPLE 2

Leptosphaeria nodorum Test (wheat/Protective

Solvent: 100 parts by weight of dimethylformamide

Emulsifier: 0.25 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound until dew-moist. After the spray coatinghas dried on, the plants are sprayed with a spore suspension ofLeptosphaeria nodorum. The plants remain for 48 hours in an incubationcabin at 20° C. and 100% relative atmospheric humidity.

The plants are placed in a greenhouse at a temperature of 15° C. and arelative atmospheric humidity of about 80%.

Evaluation is effected 10 days after the inoculation.

In this test, a clearly superior activity compared with the prior art isshown, for example, by the compounds according to the followingPreparation Examples:

                  TABLE 2    ______________________________________    Leptosphaeria nodorum test (wheat)/protective                              Degree of                 Active compound                              effectiveness                 concentration                              in % of the    Active compound                 in ppm       untreated control    ______________________________________    Tebuconazole 25           75    8 #STR48##    (I)                       O    1 #STR49##    Tebuconazole + (I)                 12.5 +       100    (1:1)        12.5    ______________________________________

EXAMPLE 3

Erysiphe Test (barley)/Protective

Solvent: 10 parts by weight N-methylpyrrolidon

Emulsifier: 0.6 parts by weight alkylarylpolyglycolether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound until dew-moist. After the spray coatinghas dried on, the plants are dusted with spores of Erysiphe graminisf.sp. hordei.

The plants are placed in a greenhouse at a temperature of about 20° C.and a relative atmospheric humidty of about 80%, in order to promote thedevelopment of powdery mildew pustules.

Evaluation is carried out 7 days after the inoculation.

In this test, a clearly superior activity compared with the prior art isshown, for example, by the compounds according to the followingpreparation examples:

                  TABLE 3    ______________________________________    Erysiphe-Test (barley)/protective                                    Degree of                           Active   effective-                           compound ness in %                           concen-  of the                           tration  untreated    Active compound        in g/ha  control    ______________________________________     ##STR50##    9                      50       0    0 #STR51##             50       15    1 #STR52##             50       85    ______________________________________    mixture according to the invention:    (I) + (ηb)   25 +   100    (1.0:1)          25    (I) + (ηa)   25 +    58    (1.0:1)          25    ______________________________________

EXAMPLE 4

Erysiphe Test (wheat) Protective

Solvent: 10 parts by weight N-methylpyrrolidone

Emulsifier: 0.6 parts by weight alkylarylpolyglycolether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are dusted with spores ofErysiphe graminis f. sp. hordei. 48 hours after the inoculation, theplants are sprayed with the preparation of active compound untildew-moist.

The plants are placed in a greenhouse at a temperature of about 20° C.and a relative atmospheric humidity of about 80%, in order to promotethe development of powdery mildew pustules.

Evaluation is carried out 7 days after the inoculation.

In this test, a clearly superior activity compared with the prior art isshown, for example, by the compounds according to the followingpreparation examples:

                  TABLE 4    ______________________________________    Erysiphe-Test (wheat)/protective                                    Degree of                           Active   effective-                           compound ness in %                           concen-  of the                           tration  untreated    Active compound        in g/ha  control    ______________________________________     ##STR53##    2                      200 25   85 30    0 #STR54##             200      79    3 #STR55##             25       85    ______________________________________    mixture according to the invention:    (I) + (ηb)   12.5 +  100    (1.0:1)          12.5    (I) + (ηa)   100 +   94    (1.0:1)          100    ______________________________________

EXAMPLE 5

Erysiphe-Test (wheat)/Curative

Solvent: 10 parts by weight of N-methylpyrrolidone

Emulsifier: 0.6 parts by weight of alkylarylpolglycolether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for curative activity, young plants are dusted with spores ofErysiphe graminis f.sp. hordei. 48 hours after the inoculation, theplants are sprayed with the preparation of active compound untildew-moist.

The plants are placed in a greenhouse at a temperature of about 20° C.and a relative atmospheric humidity of about 80%, in order to promotethe development of powdery mildew pustules.

Evaluation is carried out 7 days after the inoculation.

In this test, a clearly superior activity compared with the prior art isshown, for example, by the compounds according to the followingpreparation examples:

                  TABLE 5    ______________________________________    Erysiphe-test (wheat)/curative                                    Degree of                           Active   effective-                           compound ness in %                           concen-  of the                           tration  untreated    Active compound        in g/ha  control    ______________________________________     ##STR56##    9                      200      30    0 #STR57##             200      75    ______________________________________    mixture according to the invention:    (I) + (ηa)   100 +  96    (1.0:1)          100    ______________________________________

EXAMPLE 6

Leptosphaeria nodorum Test (wheat)/Curative

Solvent: 10 parts by weight of dimethylformamide

Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 parts by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for curative activity, young plants are sprayed with thepreparation of active compound until dew-moist. After the spray coatinghas dried on, the plants are sprayed with a spore suspension ofLeptosphaeria nodorum. The plants remain for 48 hours in an incubationcabin at 20° C. and 100% relative atmospheric humidity.

The plants are placed in a greenhouse at a temperature of 15° C. and arelative atmospheric humidity of about 80%.

Evaluation is effected 10 days after the inoculation. In this test, aclearly superior activity compared with the prior art is shown, forexample, by the compounds according to the following PreparationExamples:

                  TABLE 6    ______________________________________    Leptosphaeria nodorum-Test (Wheat)/curative                                    Degree of                           Active   effective-                           compound ness in %                           concen-  of the                           tration  untreated    Active compound        in g/ha  control    ______________________________________    known:    9 #STR58##             400      25    3 #STR59##             400      49    ______________________________________    mixture according to the invention:    (I) + (ηb)   200 +  81    (1.0:1)          200    ______________________________________

EXAMPLE 7

Pyrenophora teres Test (barley)/Protective

Solvent: 10 parts by weight N-methylpyrrolidon

Emulsifier: 0.6 parts by weight alkylarylpolyglycolether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparationof active compound until dew moist. After the spray coatinghas dried off, the plants are sprayed with a conidia suspension ofPyrenophora teres. The plants then remain in an incubation cabin at 20°C. and 100% relative atmospheric humidity for 48 hours.

The plants are placed in a greenhouse at a temperature of about 20° C.and a relative atmospheric humidity of about 80°.

Evaluation is carried out 7 days after inoculation.

In this test, a clearly superior activity compared with the prior art isshown, for example, by the compounds according to the followingpreparation examples:

                  TABLE 7    ______________________________________    Pyrenophora teres-test (barley)/protective                                    Degree of                           Active   effective-                           compound ness in %                           concen-  of the                           tration  untreated    Active compound        in g/ha  control    ______________________________________     ##STR60##    2                      25       33    3 #STR61##             25       33    ______________________________________    mixture according to the invention:    (I) + (ηb)   12.5 +  75    (1.0:1)          12.5    ______________________________________

We claim:
 1. A fungicidal composition comprising a synergisticallyfungicidally effective amount of a combination of a first compound ofthe formula (I): ##STR62## and a second compound selected from the groupconsisting of: a) chlorothalonil of the formula: ##STR63## b) fluazinamof the formula: ##STR64## and c) procymidone of the formula: ##STR65##where the ratio of said first compound of the formula (I) tochlorothalonil ranges from 1:0.5 to 1:10;to fluazinam ranges from 1:0.1to 1:10; and to procymidone ranges from 1:0.5 to 1:10.
 2. A method ofcombatting fungi which comprises administering to such fungi or to afungus habitat a synergistic fungicidally effective amount of acomposition according to claim
 1. 3. The fungicidal compositionaccording to claim 1, wherein the second compound is CHLOROTHALONIL.